Various compounds and production methods thereof have previously been known regarding a 5-methylene-1,3-dioxolan-4-one derivative represented by the following general formula (A):
wherein each of R23 and R24 represents a hydrogen atom, an alkyl group, an aryl group which may be optionally substituted, or a cyclohexyl group; or R23 and R24 may form a phenyl group or a cyclic structure of (CH2)m together with the carbon atom to which they are bound,
wherein the substituent on the aryl group is a linear or branched alkyl group containing 1 to 12 carbon atoms or a halogen atom, and m is an integer of 2 or greater.
For example, J. Organic Chemical, 57(12), 3380 (1992) and Tetrahedron Lett., 30(52), 7305 (1989) describe a method of producing the 5-methylene-1,3-dioxolan-4-one derivative via a 5-(phenylthio)methyl-1,3-dioxolan-4-one derivative obtained by reacting a compound wherein, in the above formula (A), R23 represents a hydrogen atom and R24 represents a t-butyl group or a cyclohexyl group, and β-(thiophenoxy)methyllactate, with a ketone or an aldehyde. However, the method of producing the above derivative of interest via the 5-(phenylthio)methyl-1,3-dioxolan-4-one derivative has very complicated steps in which the 5-(phenylthio)methyl-1,3-dioxolan-4-one derivative is oxidized at −78° C. using 3-chloroperbenzoic acid followed by a treatment with triethyl phosphate at 210° C.
Japanese Patent Laid-Open No. 7-70106 discloses a compound wherein, in the above formula (A), R23 represents a hydrogen atom and R24 represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group (more specifically, 2-tert-butyl-5-methylene-1,3-dioxolan-4-one). In addition, the above published application also discloses a method of producing the compound by reacting a 5-halogeno-5-methyl-1,3-dioxolane-4-one derivative such as 2-tert-butyl-5-bromo-5-methyl-1,3-dioxolan-4-one with a tertiary amine such as trioctylamine or tributylamine in a solvent such as carbon tetrachloride or cyclohexane under reflux, and carrying out a dehydrohalogenation reaction.
Japanese Patent Laid-Open No. 10-316609 discloses a compound wherein, in the above formula (A), each of R23 and R24 represents an alkyl group (more specifically, 2-tert-butyl-2-methyl-5-methylene-1,3-dioxolan-4-one, etc.). Moreover, the above published application also discloses a method of producing the compound, which comprises: reacting 2,2-disubstituted-5-methyl-1,3-dioxolan-4-one such as 2-tert-butyl-2,5-dimethyl-1,3-dioxolan-4-one, etc., which is synthesized from ketones and lactic acid, with a halogenating agent such as N-bromosuccinimide in a solvent such as cyclohexane under reflux, so as to obtain 2,2-disubstituted-5-halogeno-5-methyl-1,3-dioxolan-4-one; reacting the obtained compound with a tertiary amine such as trioctylamine or triethylamine in a solvent such as cyclohexane under reflux and carrying out a dehydrohalogenation reaction.
Furthermore, USSR Patent No. 606,313 describes a compound wherein, in the above formula (A), each of R23 and R24 represents a hydrogen atom or an aryl group, or R23 and R24 form a cyclic structure (CH2)m (wherein m represents an integer of 2 or greater). Polym. Prepr. (Am. Chemical Society, Div. Polym. Chemical), 28(1), 154 (1987) describes a compound wherein, in the above formula (A), each of R23 and R24 represents a methyl group. Japanese Patent Laid-Open No. 3-37214 discloses a compound wherein, in the above formula (A), each of R23 and R24 represents a hydrogen atom, a phenyl group having an alkyl group containing 1 to 12 carbon atoms or a halogen atom as a substituent, or an alkyl group containing 1 to 12 carbon atoms. Still further, all of the above USSR Patent No. 606,313, Polym. Prepr. (Am. Chemical Society, Div. Polym. Chemical), 28(1), 154 (1987), and Japanese Patent Laid-Open No. 3-37214 describe a production method comprising reacting β-halolactic acid with a ketone or an aldehyde to synthesize a 5-halomethyl-1,3-dioxolan-4-one derivative, and subjecting it to a dehydrohalogenation reaction with a base such as amine.
However, a 5-methylene-1,3-dioxolan-4-one derivative having a bridged cyclic hydrocarbon structure as a substituent and a production method thereof have not been reported so far.
Moreover, several polymers obtained by polymerizing monomers having a 5-methylene-1,3-dioxolan-4-one structure have been known as a water-soluble polymer, a biodegradable polymer, or the like. For example, T. Endo et al., Macromol. Chem. Phys., 202, 1602 (2001) describes a copolymer of 2,2-dimethyl-5-methylene-1,3-dioxolan-4-one and methyl methacrylate. Chin. J. Polym. Sci., 10, 350 (1992) describes a polymer of 2-phenyl-5-methylene-1,3-dioxolan-4-one.
However, a polymer of 5-methylene-1,3-dioxolan-4-one derivatives having a substituent with a bridged cyclic hydrocarbon structure has not been reported so far.
By the way, recently, in the field of microfabrication for production of a semiconductor device or a liquid crystal device, a miniaturization technique has been quickly progressed to realize high-density and high-accumulation of a device against the backdrop of the advancement in a lithographic technique. As such a microfabrication technique, the conversion of an exposure source into the light source with a shorter wavelength has generally been used. Specifically, the exposure source has been changed from the previous ultraviolet ray, as represented by a g-ray (wavelength: 438 nm) or an i-ray (wavelength: 365 nm) to a far ultraviolet ray.
Presently, a KrF excimer laser (wavelength: 248 nm) lithographic technique has been introduced in the market, and an ArF excimer laser (wavelength: 193 nm) lithographic technique, which is directed towards the conversion of an exposure source into the source with a further shorter wavelength, is being introduced in the market. Moreover, an F2 excimer laser (wavelength: 157 nm) lithographic technique is studied as a technique for the next generation. Furthermore, an electron beam lithographic technique, which is a somewhat different type from the above techniques, is also intensively studied.
As a resist with high sensitivity for such a light source with a short wavelength or an electron beam, a “chemically amplified resist” has been proposed by International Business Machine (IBM) Corporation, and at present, the improvement and development of this chemically amplified resist have been advanced vigorously.
By the way, in the conversion of the light source into the one with a shorter wavelength, a resin used for the resist is also forced to change its structure. For example, in the KrF excimer laser lithography, polyhydroxystyrene having high transparency to the light with a wavelength of 248 nm, a compound wherein the hydroxyl group thereof protected with an acid-dissociating solubility-inhibiting group, or the like are used. However, in the ArF excimer laser lithography, often the above resins cannot be used because they do not always have sufficient transparency to the light with a wavelength of 193 nm.
Accordingly, an acrylic resin or a cycloolefin resin that are transparent to the light with a wavelength of 193 nm attract attention as a resist resin used in the ArF excimer laser lithography. Such an acrylic resin is disclosed in published applications such as Japanese Patent Laid-Open Nos. 4-39665, 10-207069 and 9-090637, and such a cycloolefin resin is disclosed in published applications such as Japanese Patent Laid-Open No. 10-153864.
In particular, a copolymer of 2-methyl-2-adamantyl methacrylate draws the attention as a resist resin used in the ArF excimer laser lithography. This copolymer is described in S. Takechi et al., Journal of Photopolymer Science and Technology, Vol. 9, No. 3, 475-487 (1996) and Japanese Patent Laid-Open No. 9-73173. With regard to this copolymer, it has been reported that 2-methyl-2-adamantyl is cleaved by the action of an acid so that it acts as a positive type, and that the copolymer provides high dry etching resistance, high sensitivity and high resolution. However, such a copolymer having an alicyclic skeleton generally tends to have high hydrophobicity, and it does not have sufficient wettability to a developing solution in some cases.
Consequently, in order to decrease the hydrophobicity, several ideas have been proposed, which involve the copolymerization of a methacrylic acid derivative having a lactone structure or the introduction of a hydrophilic group such as a hydroxyl group into the alicyclic structure. For example, Japanese Patent Laid-Open Nos. 10-319595, 10-274852 and the like disclose a copolymer of a (meth)acrylic ester having an adamantane skeleton in an ester portion thereof and a (meth)acrylic ester having a lactone skeleton in an ester portion thereof. In addition, Japanese Patent Laid-Open No. 2002-82441 discloses a cycloolefin or acrylic copolymer containing a lactone structure.
However, in many cases, these acrylic resins or cycloolefin resins do not have sufficient solubility in a solvent when a resist solution is prepared. Accordingly, there may be a case where a long time is required for dissolution of the resin, or the number of the steps of the production method is increased by the generation of an insoluble matter, so that it might affect the preparation of the resist solution. Moreover, there may also be a case where these acrylic resins or cycloolefin resins do not have sufficient heat resistance. Furthermore, when these acrylic resins or cycloolefin resins are used as a resist resin, roughness of a sidewall of a resist pattern formed by patterning with an excimer laser and the subsequent development procedure, that is, line edge roughness might be generated, and consequently, a circuit width might become uneven or the circuit might be broken down, and the use of these acrylic resins or cycloolefin resins as a resist resin may bring about the possibility of the decrease in yield during the production process of a semiconductor.